Abstract
A repetitive two-step method involving the Pd-catalyzed Suzuki-Miyaura coupling of hydroxyterphenylboronic acid and the subsequent nonaflation of the hydroxy group has been developed for the synthesis of oligophenylenes. This method readily afforded o,o,p- and o,p-oligophenylenes with defined chain lengths. X-ray crystallography was employed to obtain the structure of the o,p-oligophenylene 9-mer.
Highlights
Oligophenylenes, which are composed of benzene rings connected through single bonds, have attracted considerable attention as an important class of oligomers [1,2,3,4,5]
We previously developed a method for oligophenylene synthesis via repetitive Suzuki-Miyaura coupling [20,21] of hydroxyphenylboronic acids with sebsequent triflation of the hydroxy group (Scheme 1a) [22,23]
While this repetitive two-step method realizes the facile synthesis of a variety of oligophenylenes with a specific chain length and different functional groups, it was only able to introduce one benzene unit in a single Suzuki-Miyaura coupling step
Summary
Oligophenylenes, which are composed of benzene rings connected through single bonds, have attracted considerable attention as an important class of oligomers [1,2,3,4,5]. We previously developed a method for oligophenylene synthesis via repetitive Suzuki-Miyaura coupling [20,21] of hydroxyphenylboronic acids with sebsequent triflation of the hydroxy group (Scheme 1a) [22,23] While this repetitive two-step method realizes the facile synthesis of a variety of oligophenylenes with a specific chain length and different functional groups, it was only able to introduce one benzene unit in a single Suzuki-Miyaura coupling step. We describe a new version of the repetitive two-step method, which utilizes hydroxyterphenylboronic acid 1 and enables the introduction of three benzene units in one step (Scheme 1b) By employing this method, oligophenylenes with two different types of connectivity pattern, o,o,p- and o,p-oligophenylenes, were successfully synthesized in a small number of steps.
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